Novel aroylpyrroles, their production and their use in immunologic therapy

Abstract

This invention relates to novel aroylated derivatives of pyrrole. More particularly it provides the novel naphthoyl derivatives of pyrrolyl-2-carboxylic acid having the general formula I: ##STR1## wherein: R 1 is a lower alkyl radical, a phenyl radical or a hydrogen; X is a hydrogen, a hydroxy or a methylsulphinyl group; Y is a hydrogen or together with A' a double bond; A is a hydrogen or a hydroxy; A' is a hydrogen or together with Y a double bond; B is a hydrogen or a hydroxy; B' is a hydrogen or together with C a double bond; C is a hydrogen or together with B' a double bond; C' is a hydrogen, a hydroxy or a methylsulphinyl group; with the proviso that X, Y, A, A', B, B', C and C' are not simultaneously a hydrogen. The compounds according to this invention, may exist in the free acid form or as a salt. They found a use in human or veterinary medicine in the form of pharmaceutical compositions for preventing or treating the immunological diseases.

What we claim is: 
     
       1. The naphthoyl derivatives of pyrrolyl-carboxylic acid selected from the group consisting of: (a) an acid derivative of the formula ##STR23##  wherein: X is hydrogen, hydroxy or methylsulphinyl Y is hydrogen, or together with A' forms a double bond;   A is hydrogen, or hydroxy;   A' is hydrogen or together with Y forms a double bond;   B is hydrogen or hydroxy;   B' is hydrogen or together with C forms a double bond;   C is hydrogen, or together with B' forms a double bond;   C' is hydrogen, hydroxy or methylsulphinyl with the proviso that at least one member of the group X, A, B, and   C' is other than hydrogen and one member only of the group X, and C' is methylsulfinyl or hydroxy; and     (b) the base addition of salts thereof with a therapeutically compatible mineral or organic base.   
     
     
       2. A compound according to claim 1 having the formula 1 A  : ##STR24## wherein X is methylsulphinyl group and C' is hydrogen; or X is hydrogen and C' is methylsulphinyl and   A is hydrogen or hydroxy.   
     
     
       3. A compound according to claim 1 selected from the group consisting of: (a) 5-6 dihydrodiols of the formula ##STR25## (b) and the 3,4 dihydrodiols of the formula ##STR26##   
     
     
       4. A compound according to claim 1 namely N-methyl-4-(3,4-dihydroxy-3,4,-dihydronaphthoyl-1)-pyrrolyl-2-carboxylic acid. 
     
     
       5. A compound according to claim 1 namely N-methyl-4-(5,6-dihydroxy-5,6-dihydronaphthoyl-1)-pyrrolyl-2-carboxylic acid. 
     
     
       6. A compound of claim 1 namely N-methyl-4-(6-methylsulfinyl naphtholyl-1)-pyrrolyl-2-carboxylic acid. 
     
     
       7. A compound of claim 1 namely N-methyl-4-(3-methylsulfinyl naphtholyl-1)-pyrrolyl-2-carboxylic acid.